Ethyl Acetate → HCID 58847439, compound

HRID 1272057Notes

Reaction equation

[N:1]1([C:5]([C:7]2[S:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3Cl)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH3:17][O:18][C:19](=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[Cl:28].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CS(C)=O.O>[CH3:17][O:18][C:19](=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:13]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:8]=[C:7]([C:5]([N:1]4[CH2:4][CH2:3][CH2:2]4)=[O:6])[S:15][C:14]=23)=[CH:23][C:22]=1[Cl:28]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of azetidin-1-yl-(7-chloro-thieno[3,2-b]pyridin-2-yl)-methanone (21a) (930 mg, 3.70 mmol), (2-chloro-4-hydroxy-phenyl)-acetic acid methyl ester (49e) (740 mg, 3.70 mmol), and Cs2CO3 (1.82 g, 7.40 mmol) in 7 mL of DMSO was heated at 100° C. for overnight and cooled to room temperature. EtOAc and water were added. The organic layer was washed three times with water, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with EtOAc:CHCl3:MeOH (1:1:0.04) to provide 640 mg of white solid as the intermediate 49f. 1H NMR (300 MHz, CD3OD) δ 8.47 (d, 1H, J=5.46 Hz), 7.74 (s, 1H), 7.43 (d, 1H, J=8.48 Hz), 7.32 (d, 1H, J=2.45 Hz), 7.15–7.10 (m, 1H), 6.73 (d, 1H, J=5.47 Hz), 4.67–4.54 (m, 2H), 4.24–4.13 (m, 2H), 3.80 (s, 3H), 3.65 (s, 2H), 2.48–2.33 (m, 2H). LCMS (ESI+) [M+H]/z Calc'd 417, found 417.

Workup

temperaturecooled to room temperature
washThe organic layer was washed three times with water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography
washeluting with EtOAc:CHCl3:MeOH (1:1:0.04)

Sources & evidence

ORD record: ord-92bac0733db14350b6679e5c32de0bf1
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208500B2

Reaction notes

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